


Dude looks like a Lady

by LeafZelindor



Category: Kingsman: The Secret Service (2015)
Genre: Crossdressing, Fix-It, Genderfluid, M/M, Pre-Slash, interest in women's clothing
Language: English
Status: Completed
Published: 2016-01-17
Updated: 2016-01-17
Packaged: 2018-05-14 13:27:36
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,301
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5745565
Author URL: https://archiveofourown.org/users/LeafZelindor/pseuds/LeafZelindor
Summary: <blockquote class="userstuff">
              <p>Eggsy is challenged to dress up like a girl. Harry likes it. Very much. Jamal goes into shock, and Roxy has to much fun treating Eggsy like her own personal doll.</p>
            </blockquote>





	Dude looks like a Lady

**Author's Note:**

> second work for a 52 short stories in 52 weeks.

52 stories, 52 weeks  
A story about rising to a challenge.

“You really think I can't do it?” The young man challenged, his eyebrow going up now. He considered his friend across from him. Jamal laughed at him and then threw back his shot, putting it down with a solid thunk.

“No, I think you can't.” He shot back. The blond young man smirked at his friend now and glanced at the young woman next to him. She'd become one of his best friends and she looked overly amused now.

“I don't know if you should challenge Eggsy to anything. I think he excels at any task he's given.” She responded and then tipped the jewel bright liquid in her own glass towards the blond, Eggsy. Jamal groaned now, as if he knew he might have made a dumb choice.

“Fine. I want you to do it. Roxy you can even help him.” Jamal said with a grin. He tilted his head in thought. “And I think there should be a time limit.”

“A time limit? Really?” Eggsy put his pint down and leaned towards Jamal. “Okay, What rules do you want to make on this fuckin challenge J.” His eyes were glowing, not just because he had been drinking but with excitement. He loved to blow people's minds really, and this would be just one more way.

“Fine, one week. Total transformation, I want to see you in a dress, heels, make up, hairstyle, the works. Believable Eggsy. You gotta make every straight dude in the joint's head turn.” He pointed a finger at him. It would be hilarious. There hadn't been enough to laugh about after V-day. He couldn't wait to get pictures.

“Every?” Eggsy grinned now. “You got it mate.” He knocked back the last of his pint and looked at Roxy. “Well Rox? Ready to make a lady out of me?”

“Hell yes.” His posh coworker looked as excited as he did. She finished her drink and got up, still nimble in the lovely heels she'd worn to come out with him and Jamal for drinks. “We're going to mine. You need to grab JB?”

“Nah, Mum can keep an eye on him. I'll just text her.” Eggsy fished his mobile from his pocket and composed a text carefully //sloshed, crashin on Rox's couch. Pick up JB tomorrow// He sent, not expecting a reply from his mum, he'd asked, begged her really to watch the pug for the night. Daisy loved him and Michelle looked more amused than anything over the situation. She loved the house he'd been given as Galahad though. Had made it into a real home. It was nice. He tucked his mobile away and moved to get up and go with her. “You'll be eating those words next week J.” He winked at his friend. Jamal snorted and waved them off picking his drink back up. 

Roxy laughed and looped her arm through Eggsy's as they headed out of the pub. “You sure about this Eggsy?”

“Have you ever seen me back down from a challenge?” He winked at her. She laughed and hugged his arm some more. “Besides, I've always wanted to experiment with dressing up like a girl. And you're an expert at being a lady, right Lady Morton?” He teased easily. Roxy flushed and gave him a half of a shrug.

“Fine then. Be prepared to go through hell.” She mused as she eyed him some. She had some idea's already. “You're going to wear a corset. It's the only way we'll get any curves on you, beanpole.” She hummed Eggsy laughed softly and let himself be drug towards a cab so they could go to Roxy's flat. This was going to be fun. 

It was another day and a half before Roxy had everything she wanted him to wear arranged. She'd had to go buy him a corset (hers were to small for him) and a few other things. Eggsy made a face at himself in the mirror as she laced it onto him. “Would you stop it. I told you, we need to give you some curves, just wait till you see it with the clothing. You'll see.” She started to pull the ties together properly and Eggsy's eyes widened some as he felt the way it hugged his skin, compressing about him. “Whoa.. how often do you wear something like this?”

“Not often enough. I used to a lot in school because it was fun. In Kingsman though it's very impractical. Restricts my movements to much.” She admitted as she fitted it. “How does that feel? Can you breath all right?” She asked. He'd thought she'd pull it tighter, but he could see a soft curve to his sides really and he took a slow breath, testing it.

“Yeah fine.” He agreed now. Roxy nodded and carefully tied off the strings now. “Why not any tighter? I hardly feel like you pulled it that tight?”

“Like I'd let you hurt yourself with it? If we had proper time you'd season it and we'd be able to pull it more snug but I am not going to let you do anything rash. This will work. You'll see.” Roxy smiled and gave his arse a swat making Eggsy yelp and glare at her. She grinned broadly though and moved to get everything else, A water bra he saw, his eyebrow going up, but he pulled it on carefully and she showed him how to latch it. Then proceeded to the slip and other items, including a rather lovely black dress with large roses on it, it was aline with a top that wrapped around his shoulders, and helped accent the fake breasts Roxy had given him. He also was in proper stockings and heels. He felt wobbly in them and they weren't even that tall, only two inches, and chunky she called them. He felt like it was a huge change though. 

“What the hell Rox! How do you girls do this all the time?” He asked as he took a few steps carefully. Roxy laughed softly at him.

“You'll get good. We'll keep moving around with them.” She said with a nod, approving really. “Be careful, step heel to toe, and don't take big steps, little ones. It's more graceful that way.”

Eggsy nodded and listened, carefully stepping as she told him. They just walked around the flat now. Her poodle watching them curiously. It was a good thing JB wasn't here or Eggsy would trip over him probably. He was careful though. It got easier as he practiced. Roxy showed him the accessories she'd chosen for his outfit. And the wig she'd gotten. It was just past his shoulders, blond, curly, matched his own hair almost perfectly for shade really. This transformation was, exciting really. He touched the strands of hair a moment or two slowly.

“You look pretty happy you know.” Roxy said two days later. She'd done his make up, he was in the whole outfit. He'd been practicing with the heels every day, always at her place he didn't want his mom thinking anything to odd. Though he rather liked it.

“Ah...You know I was always, curious about wearing girls things. But with my step-dad..' He trailed off and shrugged some. He paused to look at himself in the mirror. She'd done his make up lightly but it was amazing how much a little make up transformed his face. He felt completely more feminine like this. The soft swish of the dress (He was getting very fond of the one she'd picked out for him) around his legs, the way everything was gently accented by the fabric clinging to his body. The corset had gotten a bit more comfortable over the days of practice too. She assured him that was normal. He glared as he saw her tuck her mobile away.

“Hey, I'm taking pictures. It's not blackmail, you look better than most girls right now.” She grinned at him. Eggsy rolled his eyes at that and then turned himself around neatly and practiced folding his hands together lightly. “So what are we really practicing today?” He asked now. 

“Actually now that i've prettied you all up you're going to take a shower.” Roxy said with a smirk. Eggsy blinked at her, confused.

“A shower? I took one this morning….” He started then Roxy smirked and held up a can of woman's shaving cream and a razor. “…..You want me to shave?”

“Yup, Legs and underarms.” She grinned devilishly now at him. Eggsy's eyes widened quickly now. “I mean it. You're playing a part, you have to play it right.” She wiggled the items. “And I'll show you how best to take off the make up.” She moved towards her bathroom. “You can leave things out here. My robe is next to the wardrobe.”

Eggsy was left to carefully take off the shoes and stockings. Then he put the wig on the stand she'd provided him. He twisted his hand back carefully to unzip the dress gently and quietly. Once he'd wiggled out of it he hung it up on it's hanger, smoothing the fabric out. Roxy was going to have to help him out of the corset like usual, but he was hardly body shy around her. He was almost fully undressed when he joined her, laughing soflty at the sight of his delicately painted face in the mirror with his short hair. Roxy grinned at him and handed him several things, showing him with empty hands what to do so he could clean his face himself. He hummed quietly. “You'll teach me how to do the make up myself yeah?”

“If you want to keep doing this beyond this little challenge, of course Eggsy.” She admitted with a nod. Otherwise she was happy to do his make up for him. He hummed quietly and then waited for her to unlace the corset enough for him to take it off.

“I might.” He admitted. “We'll see.” He was enjoying it so far. Not quite confident for the end of the week yet, but he was getting there. He sighed and moved to start her shower up, eyeing the razors, she'd actually left him more than one! And the cream.

“When you get out we'll put some lotion on your skin too. You'll see.” Roxy coaxed. She winked and moved to get herself a drink. “Get on in now.”

“Bitch.” He said affectionately and then got himself into the shower. Following her water clouded instructions. He even washed himself off with her lightly floral body wash. She never wore anything to heavy in their line of work, it smelled nice though. He tackled his underarms first, the hardest, considering how long the hair was. But after some work they were smooth, it felt a little weird when he brought his arms down. He leaned over to smooth the shaving cream over his legs now. This felt really odd. It would soon feel even more strange. He carefully worked on shaving his legs, around his knees. He nicked the skin once or twice, earning a curse that made Roxy giggle a bit. It took far longer than he thought to get this done, never again would he accuse Roxy of taking to long in the shower.

Roxy offered him a towel when he got out of the shower. He accepted it and carefully toweled himself off now. His skin felt, colder somehow. That was interesting. Roxy held up a bottle of lotion now. “Put it on your legs especially but you can do anywhere else you want.”

“Anywhere?” He teased and she swatted him with it, rolling her eyes. Eggsy stole it from her hand though and then settled in. He'd seen his mum put lotion on her hands sometimes, he had an idea of what to do already. He carefully smoothed the lotion into his legs. It felt odd, the cool cream, and how smooth his skin was. Roxy grinned softly and moved to retrieve something, offering a skirt to him when he was done. Eggsy eyed her a bit. “What'd you buy me a whole wardrobe?”

“No, just a few things in case you decided you wanted to do this more often.” She teased. “Now put the skirt on. I want you to feel the difference.”

“Fine Fine.” He pulled his pants back on before he put on the skirt. This was longer than the dress, reaching about mid calf on him. Eggsy blinked as the fabric brushed his skin. He then shifted and twisted a bit, his eyes widening. “Holy shit….”

Roxy giggled and watched as Eggsy walked out to the mirror to look, and then pulled up the skirt to rub his leg some. “holy fucking shit. Roxy….”

“Feels good doesn't it?” She grinned softly. “Friday you'll want to make sure you shave again before we dress you up proper.” She'd already discreetly asked a few people to show up at the pub who were not originally in on this challenge, like Merlin and Harry, who was still recovering from his injuries taken in America and was not back on active duty, though he'd been voted in as Arthur officially. She couldn't wait to see how they reacted to Eggsy's transformation. 

“Aces Rox..” He breathed as he for a bit longer stroked his own skin, mesmerized by it. She was delighted with how Eggsy was feeling. The transformation was almost complete. She settled him down and helped him try a few more things, practicing things which were normal for girls, how to cross his legs, sit up straight, talk quietly and politely, fluttering eyelashes.

By the time Friday rolled around she was more than confident that Eggsy was going to pull this off. She helped him get ready for the evening. He came over early, showering, shaving, dressing. She applied his make up carefully and made sure his wig was in place correctly. The Eggsy that had walked into her flat a few hours ago was not who walked out. “You look gorgeous Elaine” She winked at Eggsy. He lightly wrinkled his nose at the name she'd chosen and then chuckled a little. They made their way down to the waiting cab and were soon on their way. Merlin had sent her a text confirming he'd convinced Harry to come to the pub. She was very much looking forward to this. If Eggsy could turn Harry's head like this, well then he'd been more than successful in the challenge Jamal had given. 

“I'm going to send you in first.” She said. If she went in everyone would know immediately that it was Eggsy. Instead he'd go in first, and they'd see what happened. She'd only be about ten minutes behind. Eggsy nodded quietly and then moved to get out of the cab carefully. He adjusted his skirts lightly and grasped the clutch she'd given him, straightening some and making his way for the door. He let himself into the pub and glanced around, almost freezing as he caught sight of Merlin and Harry at one of the far tables, where they could see the rest of the room easily. However there was a stir now, people glancing at him, men especially. Eggsy let his eyes drop just a little, trying not to blush at the attention. Did all girls feel like this when they entered a room? He moved towards the bar to order a drink, Roxy had suggested one she though he'd like. He realized halfway there that Harry was watching him, closely. However a young man at the bar offered to pay for Eggsy's drink when he ordered, he managed to thank him quietly, pitching his voice just a little higher. Drink in hand he easily sat himself on the stool, making sure to cross his legs properly and took a sip, eyes flicking around the room. Merlin had said something to Harry. Who muttered something back, but his eyes were on the newcomer. It was a little intimidating. How Harry watched him.

Roxy wandered in, ignoring Eggsy in favor of going to join Jamal who seemed confused she was alone. She grinned at him now. Jamal eyed her warily. She looked far to pleased. Then cocked her head. “NO fucking way.” Jamal exclaimed. He turned to look at Eggsy then back at her. “Holy shit.” He breathed out. Roxy winked at Eggsy and he grinned softly, moving to get up and walk over to join them.

“Well? How do I look?” He asked as he placed his glass down gently and tilted his head.

“….fucking hot.” Jamal said, his eyes wide. “I didn't think you'd fuckin do it!”

“Well, you did challenge me.” Eggsy moved to sit, fixing his skirts properly, making sure to sit up straight still. He saw a realization cross Harry's face, a flicker of surprise, but.. the interest in his eyes didn't leave. Oh, that was interesting. He quietly took a drink again quickly, busying himself with it, quietly and teasingly razzing Jamal for not believing that he could do this. Another young man offered to buy him a drink, he shared a look with Roxy who grinned and accepted quietly but refused to leave his friends to join the other young man. Harry finally said something to Merlin and got up. Eggsy couldn't help watching him move, he used the flash lashes Roxy had put on him to help shade where his eyes were looking though. 

Harry moved from where he'd sat with Merlin to the table where the younger people sat. “Roxy, you haven't introduced me to your friend.” He said, all charm and politeness. Jamal about choked on his drink now.

“Oh Harry, this is Elaine.” Roxy smiled quietly. “Elaine, this my boss, Harry Hart.” She watched as Eggsy's cheeks colored now, brighter than the light amount of blush that she'd put on him had. Eggsy took a breath and looked up now. Harry reached out and gently lifted Eggsy's hand, kissing the back of it now.

“It's a pleasure to meet you, Elaine.” Harry murmured, his eyes looked delighted now, and there was something else. The scar prickling his brow wrinkled somewhat, adding to his, already good looks. Eggsy took a breath now.

“And you.” He responded breathily now. As if he really was Elaine. Harry smiled a little more broadly now.

“Could I buy your next drink?” Harry charmed now. Eggsy swallowed and then nodded slowly. Harry moved his hand to brush the hair off his shoulder a moment. “I'll be back.” He winked and moved towards the bar now. Merlin looked beyond amused. Jamal's mouth was hanging slightly open. Roxy had chosen to bury her face in her drink to keep herself from giggling too much. It was about time.

It really wasn't to much of a surprise when Eggsy and Harry left together a few hours later.

“Is this going to be a new habit?” Harry asked, his lips pressed just below Eggsy's ear, he'd gotten the dress off of the lovely young man, his hands were settled at his hips. Eggsy just leaned back against him. “Because I have a few ideas for… Elaine.”

“Well, in that case.” Eggsy chuckled softly, He turned now to look up at Harry though. “Maybe...But um.. I don't plan to get a sex change.”

“Oh good, because I rather like you as you are.” Harry rumbled as he pushed Eggsy towards the bed now. “But I wouldn't object to seeing you like that again.” He rumbled as he moved to crawl over him, and show Eggsy exactly how much he had enjoyed seeing him like this, and how much he wanted him just the way he was too.

**Author's Note:**

> Eggsy's dress for those who can't quite picture it http://imgur.com/4AG0RO7


End file.
